DE2848224A1 - WEED KILLERS, METHODS FOR PRODUCING AND USING THEM TO CONTROL UNWANTED PLANT GROWTH - Google Patents

Description

1.11.78

Applicant: MEIJI SEIKA KAISHA, LTD. 4-16, Kyobashi 2-chome, Chuo-ku, Tokyo, Japan

Inventor: Tetsuo TAKEMATSU: No. 612, Mine-machi, Utsunomiya-shi, Tochigi-ken, Japan Makoto KONNAI: No. 3645, Tsuruta-machi, Utsunomiya-shi, Tochigi-ken, Japan Kunitaka TACHIBANA: No. 6, Isogo 3-chome, Isogo-ku, Yokohama-shi, Kanagawa-ken, Japan Takashi TSURUOKA: No. 1, Kawara-cho, Saiwai-ku, Kawasaki-shi, Kanagawa-ken, Japan Shigeharu INOUYE: No. 16-2, Tsutsujigaoka, Midori-ku, Yokohama-shi, Kanagawa-ken, Japan Tetsuro WATANABE: No. 390-3, Matsumi-cho 2-chome, Kanagawa-ku, Yokohama-shi, Kanagawa-ken, Japan

Representative: Dipl.-Ing. Meissner, Hans Dipl.-Ing, Bolte, Erich patent attorneys,
Sievogtstrasse 21,
D-2800 Bremen 1
Federal Republic of Germany

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Weed killers, procedures for the production of the same and their use to control undesirable vegetation

The invention relates to weed killers,

a method for producing the same as well as their

Use to destroy unwanted vegetation.

All previously known substances that are effective as herbicides or weed killers are chemical synthetic compounds that in some cases cause difficulties in terms of Cause pollution. In view of the increasingly strict legal regulations In addition to environmental pollution, it is becoming more and more urgent to find weedkillers that can be used on The place where they are used are rapidly degraded and do not cause environmental pollution.

In Japanese Patent 827,768, U.S. Patent 3,832,394 and German Patent 2,236,599 is the antibiotic SF-1293 and a microbiological process for its production the same protected. It has now been found that the antibiotic SF-1293 works as a herbicide able to meet all of the above requirements because it is a metabolic product in the material cycle that takes place in nature inserts and decomposes into harmless substances

25 falls.

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The antibiotic SF-1293 - also as a substance SF-1293 or simply referred to as SF-1293 (in the form of the free acid) of the following general formula:

p-ch ^ -ch ^ ch-conh-ch-conh-ch-cooh

^H0 'NH.

CH, Cf

· In the aforementioned U.S. patent as well as the German patent also mentioned, it is already mentioned that the substance SF-1293 against various fungal diseases of plants including Pellicularia sasakii (vaginal dry rot in rice) and Piricularia oryzae (rice pest) is highly effective.

As a result of further studies of the biological effects and possible uses of SF-1293 has now been found that this substance has a strong herbicidal effect excels when it is used in an amount which is about 10 times higher than the amount at Use as a fungicide. It has been shown that SF-1293 and various salts of this compound effective herbicides for growing annual and perennial weeds, as well as for various bushes and trees - and represent this when the leaves are treated; they are capable of the above-ground parts of the Difficult to damage or kill plants and, to a large extent, offspring of plants from the prevent underground parts.

Accordingly, it is an object of the present invention the use of the antibiotic or the substance SF-1293 or salts of this compound as

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Herbicide which, when applied to unwanted plants or their growth medium, inhibits growth of the plants severely hindered or kills the plants entirely.

The substance SF-1293 in the form of the free acid and its salts (hereinafter collectively simply as Substances designated SF-1293) prevent growth unwanted plants or kill these unwanted plants, both when applied directly on the plant (application after emergence) as well as when applying to the ground or another Growth medium in which the plants grow, so that seedlings of the plants are prevented from emerging will (use before rising).

The substances SF-1293 according to the present invention have the advantage that they can be used at the optimal time at any time of the year and that it can be used not only as a contact herbicide, but also act as a systemic herbicide that interferes with the plant metabolism. They have in addition, the only favorable characteristic that it is compared to the wood plant Chamaecyparis obtusa (Japanese cypress, Japanese name: "hinoki"; a plant that provides a wood, which in considerable Scope used in the construction of furniture and houses) do not have a phytotoxic effect. Nevertheless, they are highly toxic to unwanted bushes and weeds, that grow in the area in which the desired wood plants occur naturally or artificially

30 can be activated.

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According to a preferred embodiment of the invention, the substances are SF-1293 for selective destruction of weeds and bushes in the growth area of Chamaecyparis obtusa ver-5 turns.

In more recent times, the question of the prevalence of exotic and naturalized weeds as well as perennial Weeds gained importance. To prevent the growth of these weeds one has hitherto N-phosphonomethylglycine (which is generally available under the Name glyphosate is known) is used. It could now be determined that the substances SF-1293, which act similarly to glyphosate, of this compound in terms of herbicidal properties and the spectrum of effects in weed killing are far superior. The substances SF-1293 are effective in lower concentrations than glyphosate, show the herbicidal effects faster than this and act against a wider range of plants than this; in addition, there is their absolute harmlessness compared to Chamaecyparis obtusa, which has already been pointed out. Glyphosate, on the other hand, shows a strong Phytotoxicity to Chamaecyparis obtusa. Finally, it should also be pointed out that Glyphosate has a much lower effect on broad-leaved weeds and perennial weeds how Rumex japonicus and Cayratia japonica unfold. The substances SF-1293, on the other hand, are the same Wise and with the same application amount against all weeds of any kind, effectively and completely suppresses the offspring of perennial Weeds.

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In general, it spreads into uncultivated land, orchards, woodlands, and pastureland Annual and perennial weeds and various types of bushes quickly emerge. About growth Keeping the same under control is either a single application of a mixture of two or more herbicides or the successive multiple applications of different or the same Herbicides required. Both ways of working are

10 difficult and disadvantageous in terms of so

associated costs and efforts. The substances SF-1293 are against almost all weeds, bushes and trees with the exception of Chamaecyparis obtusa effective, so that one of the substances is used alone SF-1293 destroys all unwanted plants including weeds and unwanted trees can be. In addition, the substances SF-1293 enable the offspring or recovery of the undesired ones Prevent plants from meaning that they are actually of extraordinary herbicides for practice Represent value. The substances SF-1293 can therefore be used in an effective manner in preparation of woodland during afforestation, to control the soil weeds, which in woodland, in the Chamaecyparis obtusa is pulled, grow, to control the weeds and bushes in the pastureland, for control the ground weeds in orchards and to prevent weed growth in non-agricultural used country. They are also suitable for treating uncultivated fallow land before plowing, taking advantage of their property that they are relatively quick in the ground be inactivated. The substances SF-1293 are also used for targeted weed killing in agricultural applications used land as well as in lawns,

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interspersed with harmful perennial weeds are suitable.

The substances SF-1293 according to the present invention are generally used in the form of a mixture, in which they are present as an active ingredient together with a liquid or solid diluent or carrier material.

The active ingredient in the mixture can constitute from 0.01 to 50 percent by weight. Before use as a herbicide, the mixture is generally diluted with water to a concentration of 0.05-5%, based on the active ingredient.

The salts of substance SF-1293 that can be used as the active ingredient in the mixtures include the alkali metal salts, the alkaline earth metal salts, the salts with divalent metals, unsubstituted or substituted ammonium salts, as well as acid addition salts, which correspond to the following general formula:
P.

Η, α

J-CH ₀ -CH ₀ -CH-CONH-Ch-CONH-CH-COO (M ² )

I I

NH ₂ - CH ₃ CH ₃

n / A

1 2

In the formula, M and M, which can be the same or different, each represent a hydrogen atom or a cation such as sodium, potassium, lithium, copper, magnesium, calcium, zinc, nickel and manganese, or an ammonium cation which is either unsubstituted or substituted by one, two, three or four lower ones Alkyl, hydroxyalkyl (especially hydroxyethyl)

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or alkenyl groups are substituted; A means one inorganic or organic acids such as hydrochloric acid, sulfuric acid, hydrobromic acid, phosphoric acid, Perchloric acid, nitric acid, acetic acid, propionic acid, citric acid, tartaric acid, monochloroacetic acid, Trichloroacetic acid and trifluoroacetic acid; η means 0, 1/2 or 1; ρ means the opposite

-ι
The numerical value of the valence of M and q is the inverse

ρ is the valence of M.

The preparations according to the invention can be in the form of aqueous solutions, wettable powders and dusts, Emulsions, granules or granules are present, the active ingredient each with a suitable Diluent or carrier material is mixed. The solid preparations can be in the form of dusts or granules. Suitable solid diluents in this case are kaolin, clay, bentonite, Kieseiguhr, dolomite, Calcium carbonate, talc, powdered magnesium oxide, Fuller's earth, gypsum, Hewitt's earth, diatomaceous earth and

20 vermiculite.

The solid preparations can also take the form of dispersible ones Have powders or grains, which then contain a wetting agent to make the powder or dispersion To facilitate grains in liquids; they can also contain fillers and suspension aids.

The liquid preparations include aqueous solutions, dispersions and emulsions which are produced can by placing the active ingredient (s) in an organic solvent, which is preferably a wetting, dispersing or emulsifying aid contains, dissolves and the mixture obtained

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is then added to water, which also contains a wetting agent, dispersant or emulsifier can. Suitable solvents are acetone, isopropyl alcohol, propylene glycol, diacetone alcohol, benzene, Toluene, kerosene, methylnaphthalene and cyclohexanone.

By adding other additives that improve distribution, adhesion and resistance To improve against rain on treated surfaces, the various preparations can be even better for the suitable for various purposes.

The preparations according to the invention can optionally also other herbicides and / or plant growth regulators known per se, for example germination preventive agents containing, whereby the herbicidal effect emanating from the substances SF-1293, is increased and extended over a longer period of time.

The preparations according to the invention can also be in a liquid form for use as a spray suitable is. These are generally aqueous dispersions or emulsions that the active Component in the presence of one or more wetting agent (s), dispersing agent (s), Contain emulsifying agent (s) or suspending agent (s). These funds can be cat-

ionic, anionic, non-arfionic or amphsiAt-

be of a natural nature.

g (S & .n c ' s: c / |

Suitable cationic agents are quaternary ammonium compounds such as cetyl trimethyl ammonium bromide and alkyl pyridinium chloride. Suitable anionic agents are soaps, salts of aliphatic monoesters of sulfuric acid (e.g. sodium lauryl sulfate) and salts

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of sulfonated aromatic compounds (e.g. sodium dodecylbenzenesulfonate, sodium, calcium or ammonium lignosulfonate, butyl naphthalene sulfonate and a mixture of sodium diisopropyl and triisopropyl naphthalene sulfonates). Suitable nonionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol or cetyl alcohol or with alkyl phenols such as octyl phenol, nonyl phenol and octyl fresol. See other suitable non-ionic Medium are the partial esters derived from long-chain fatty acids and hexitol anhydrides, the condensation products of these partial esters with ethylene oxide and lecithins. Suitable ampholytic The agents are alkyldimethylbetaine and dodecylaminoethylglycine. Suitable suspension auxiliaries are hydrophilic Colloids (e.g. polyvinylpyrrolidone and sodium carboxymethyl cellulose) and vegetable smolder (e.g. gum acacia and gum tragacanth).

The preparations to be used as aqueous dispersions or emulsions are generally used delivered in the form of a concentrate which contains a high proportion of active ingredient. This concentrate must be diluted with water before use. These concentrates also need to be over can be stored well for longer periods of time and can be easily diluted with water even after such storage, so that homogeneous aqueous preparations are obtained which can be produced without difficulty with conventional spray devices can be applied.

The substance SF-1293 can, as in US Pat 3,832,394 and German patent specification 2,236,599, produced by a microbiological process According to this procedure, a die

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Streptomyces strain producing substance SF-1293 hygroscopicus grown under aerobic conditions, producing the substance SF-1293 and transforming itself into the culture broth accumulates, from which it can be separated. More typically, the substance SF-1293 producing Streptomyces hygroscopicus strain is that designated Streptomyces hygroscopicus SF-1293 Strain, which is registered in the "American Type Culture Collection" under ATCC No. 21705 and in the Japanese public depository "Fermentation Research Institute" under FERM-P No. 996 has been. The salts of the substance SF-1293 can be prepared in any known manner will.

The quantities in which the substances SF-1293 must be applied in order to be able to control or destroy them of unwanted vegetation depend both on the plant species and on the individual case selected active connection as well as climatic Conditions. In general, however, the compounds are used in amounts of 25 g to 3000 g per

10 Ar, i.e. used per 1000 m. Through trials could be found that particularly beneficial effects in the weed killing are achieved if

2 the amount applied is about 100 1 per 1000 m and the liquid preparation when used on weeds with a height of less than 10 cm 0.01 to 0.05 wt .-% of active ingredient and when used on weeds with a height of 10 to 30 cm contains 0.05 to 0.2 % by weight of active ingredient.

The substances SF-1293 act, as already mentioned at the beginning, not only as a contact herbicide, but also also as a systemic herbicide, which is found in the

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Plant metabolism is incorporated, whereby a prevention of the offspring is achieved, which in turn is extremely important for the control of perennial weeds as well as perennials and bushes.

To take advantage of the inherent benefits of substances SF-1293, maximum use, it is advisable to use them in combination with one or more known herbicide (s) or to use other biologically active substances, especially in combination with one or more systemic herbicide (s) or relatively slow acting herbicides.

It is therefore considered according to the invention, the substances SF-1293 in combination with a or more of the following substances: Choline salt of maleic acid hydrazide (hereinafter referred to as CMH denotes); Phenoxy herbicides; Benzoic acid herbicides; 2,3,6-trichlorophenylacetic acid (hereinafter referred to as TPA denotes) and their salts; ((3,5,6-Trichloro-2-pyridyl) -oxy) -acetic acid (hereinafter referred to as Dowco-233) and their salts; N-phosphonomethylglycine (commonly known as glyphosate) and its salts; Ethyl carbamoyl phosphate (hereinafter referred to as DPX-1108) and its salts; 2- (i-Allyloxyamino) -butylidene-5,5-dimethyl-4-methoxy-carbonyl-cyclohexane-1,3-dione (hereinafter referred to as NP-48); 3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea (hereinafter referred to as Linuron); 3-Amino-1,2,4-triazole (hereinafter referred to as ATA denotes); Cholinej diethylamine.

The phenoxy herbicides include, for example, 2,4-di-chlorophenoxyacetic acid (hereinafter referred to as 2,4-D) and their salts, allyl esters and ethyl esters, 2-methyl-4-chlorophenoxyacetic acid (hereinafter referred to as

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MCP) and their salts, allyl esters and ethyl esters, a- (3,4-dichlorophenoxy) propionic acid (hereinafter referred to as 3,4-DP) and their salts, d, 1-2- (2-methyl-4- chlorophenoxy) propionic acid (hereinafter referred to as MCPP) and its salts, v ^; - (2-methyl-4-chlorophenoxy) acetic acid (hereinafter referred to as MCPB) and its salts, d, l-2- (2,4,5-trichlorophenoxy) propionic acid (hereinafter referred to as 2,4,5- T) and their salts as well as α- (4- (3,5-dichloro-pyridyl-2-oxy) -phenoxypropionic acid (hereinafter referred to as SL-501) and their salts.

The benzoic acid herbicides include, for example, 2,3,6-trichlorobenzoic acid (hereinafter referred to as TBA) and its salts, 3,6-dichloro-2-methoxybenzoic acid (hereinafter referred to as Banvel-D) and their salts and 3-amino-2,5-dichlorobenzoic acid (hereinafter referred to as amibi) and their salts.

Cholines include choline itself and the salts of choline with inorganic acids such as hydrochloric acid, Phosphoric acid and carbonic acid or with organic acids such as acetic acid, oxalic acid and Ascorbic acid.

The diethylamines include diethylamine itself and its salts with inorganic or organic Acids, which can be the same as those mentioned for the choline salts.

The salts of the substance SF-1293 »those with the above Listed components can be used, correspond to the general formula (i), which above has been specified.

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By combining the substances SF-1293 with synergistic and relatively slow-acting herbicides can significantly increase their Achieve effect.

From Table 8 contained below, it can be seen, for example, that when applying 100 1 per

1000 m of a solution that contains the monosodium salt of the substance SF-1293 alone in a concentration of 0.05.%, A kill of Rumex obtusifolius (one of the broad-leaved weeds) of about 50% is achieved, but that this suppresses the offspring Weeds cannot be reached. When applying 100 liters per 1000 m of a solution which contains 2,4-D in a concentration of 0.1 % , one achieves

15 just a bending of the stems and foliage of

Rumex obtusifolius, however, has no effect regarding the killing or suppression of the offspring of these weeds. In contrast, one achieves

• 2 during the application of 100 1 per 1000 m of a solution containing a mixture of the monosodium salt \ ron SF-1293 dissolved in 0.05% concentration, and 2,4-D in 0.1% concentration, a much stronger effect than with the monosodium salt of SF-1293 alone, namely a complete kill of the above-ground parts of the plant and no offspring from the subterranean parts of the plant. The same observation could be made with Zoysia japonica, which is one of the grassy perennial weeds. When applying a solution containing the monosodium salt of SF-1293 in 0.1% concentration, about 50% destruction of Zoysia japonica is achieved, but the offspring takes place to such an extent that three months after the treatment there is no longer any difference to the untreated area. When applying a solution containing the 2,4-D in

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0.1% concentration, there is only a very slight effect or no effect at all on the grass-like plants. On the other hand, when a solution is applied that contains a combination of 0.1% of the monosodium salt of SF-1293 and 0.1 % 2,4-D, a complete kill and a complete suppression of the offspring are achieved even three months after the treatment apparently due to the synergistically increased effect of the monosodium salt of SF-1293

10 is. The combined use of SF-1293 and one

biologically active substance with auxin effect (for the ' 2,4-D is a representative representative) leads to a significant improvement in both the contact herbicidal effect as well as the systemic effect of the substances SF-1293 against broad-leaved perennial weeds and grass-like perennial weeds, so that the offspring of these weeds is also prevented with certainty.

Correspondingly remarkable improvements could be made can be achieved if CMH, which is also a known

20 th anti-auxin is, in combination with the substances

SF-1293 is used; this is explained in Examples 9 to 15 contained below. While at Use of CMH alone will only determine a weak herbicidal effect against weeds in the growth stage can, the combined use of CMH and one of the substances SF-1293 leads to a characteristic improvement both the contact herbicidal effect and the systemic herbicidal effect. Example 9 works show that the combined use of the substances SF-1293 in 0.05% concentration and of CMH in 0.3% Concentration to improve both the contact herbicidal effect (in an evaluation 21 days after treatment with the herbicide)

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as well as the one-offspring-suppressing effect (with the evaluation 4 months after treatment with the weed killer was carried out), for comparison, the treatment with the substances SF-1293 alone in 0.1! & Lger concentration is used became. In general, the effect of the substances SF-1293 increases when used in combination with CMH by twice, possibly four to five times.

10 It was also found that other

Biologically active compounds are able to improve or increase the effect of the substances SF-1293. In this way, a synergism with the compounds listed above could be demonstrated, which is also clear from Table 8 contained below.

The substances SF-1293 are also effective against a large number of weeds when used in combination with the Compounds leading to a synergism can be applied, which is evident from the examples contained below 11 to 15 can be seen. To make the substances SF-1293 have an optimal effect in terms of suppression of the offspring of perennial weeds develop, it is necessary that they develop after application on the foliage of the weed plants, but before they are killed, in the subterranean parts of the plants hike. When treating plants like Calystegia hederacea, which are very sensitive to contact herbicides it is difficult, for example, to prevent offspring from the subterranean parts of the plant, because the foliage is killed before the substances SF-1293 enter the underground parts the plant can migrate. In the case of the combined

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Turn of the substances SF-1293 together with one of the The compounds listed earlier can achieve this migration into the subterranean parts of the plant and so, to a considerable extent, offspring of plants like Calystegia hederacea from the underground parts of the plant ". From all of the above Compounds that synergistically increase the effect of the substances SF-1293 are provided by CMH in combination the best results with the substances SF-1293, which is evident from Examples 11 to 15.

It is known that CMH affects the offspring of perennials Can suppress weeds when applied to plants in autumn (see Japanese Patent Prior Publication No. 55835/76). In practice, this has the disadvantage that CMH is only applied in autumn and that the aerial parts of perennial weeds must be removed when CMH should be applied in spring or summer as a herbicide. In contrast to this Disadvantage of using CMH alone can cause CMH in a mixture with the "substances SF-1293" to others Seasons are applied as autumn because the last gradually the above-ground parts of the plant kill, so that both CMH and the substances SF-1293 migrate into the subterranean parts of the plants can and here develop their synergistic effect, so that there is a complete suppression of the offspring of these weeds. Through the combined use of CMH and the substances SF-1293 the offspring-preventing effect of CMH can be better exploited and there is the possibility of that To use CMH at all times of the year, which greatly increases its applicability in general.

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Finally, it must be mentioned that the substances SF-1293 do not show any phytotoxic effects against a timber tree, namely Chamaecyparis obtusa. This plant is found in 25 % of the forest area in Japan. CMH is also not toxic to this plant. When a weed killer, which consists of a mixture of the substances SF-1293 and CMH, was applied to an area overgrown with Chamaecyparis obtusa (Japanese cypress), an effective prevention of the growth of undesirable plants, in particular perennial weeds and bushes, which were simultaneously in the named area grew. In addition to CMH, DPX-1108, choline and diethylamines are also non-toxic to the aforementioned cypress.

The mixtures of the substances SF-1293 and the synergistic effects that increase with them known compounds mentioned above can be used as weed killers on agricultural purposes used land, woodland, pasture land, orchard land, and land not used for agriculture exactly as described above for the substances SF-1293 alone. The mixtures can also be used in bodies of water to control and suppress weeds and algae growing in the water as well as in underwater rice fields after the harvest of the ripe rice plants.

The ratio of the substances SF-1293 (A) to the compounds that develop a systemic effect with them (B) can vary within a wide range, depending on the type of compound selected (B) and the goal to be achieved with the mixture. In general it can be said that the mixing ratio between 1: 0.2 and 1:20 (by weight)

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can. The usual weight ratio of the substances SF-1293 to various compounds from the group (B) results from the following table 1.

The total amount of the substance SF-1293 (A) and the compounds (B) in the weed killers according to the present invention can generally be in the range from 0.05 to 80% by weight, based on the total preparation. In use, the preparation is generally diluted to such an extent that the concentration of the active ingredient is from 0.05 to 5% by weight. The amount in which the substance SF-1293 is applied to the area to be treated is generally from 25 to 1500 g per 1000 m ² .

The mixtures of the active compounds given in Table 1 in the concentrations given there were in an amount of 25 to 250 liters, preferably

P applied 50 to 150 liters per 1000 m.

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Table 1

active component : CMH Mixing ratio
nis Concentration (%)
in the applicable to
sentence 1-1.0 SP-1293 : 2,4-D 1 : 0.2-1.0 It : MCP 1: 1.0-20.0 Il : 3,4-DP 1: 0.3-8.0 . Il It : MCPP 1: 0.3-5.0 . It
β Il : MCPB 1: 0.5-8.0 Il
β Il : 2,4,5-T 1: 0.3-5.0 : " Il : SL-501 1: 0.3-5.0 Il
β It : 2,3,6-TBA 1: 0.3-5.0 : " Il : Banvel-D 1: 0.5-10.0 . ti It : Amiben 1: 0.3-5.0 . It
■ Il : TPA 1: 0.3-5.0 : " Il : Dowco-233 1: 0.3-5.0 > It
• Il : Glyphosate 1: 0.3-5.0 ί 0.02-0.2 Il : DPX-1108 1: 0.2-6.0 : Ο _; Ο3-Ο, 5 Il : NP-48 1: 0.3-5.0 ϊ 0.1-0 _; 6th ti : Lynuron 1: 0.5-10.0 : Ο _; Ο5-Ο _; 5 Il : ATA 1: 0.5-10 ^ 0 . Il Il : Choline 1: 0.5-10.0 ο Il Il : Diethylamine 1: 0.3-5.0 : 0.01-0.8 ti 1: 1.0-2.4 * : 0.01-0.5 Il 1: 1.0-2.4 * 0 _; C. ti Il Il Il Il Il Il Il Il Il It Il ti Il Il M. Il Il Il Il

an asterisk (*) indicates the molar ratio

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The amount of Substance SF-1293 needed will kill lim perennial weeds and bushes or to prevent their regrowth depends on the climatic conditions of the Um-5 · ' environment, for example on the temperature and the light intensity. The desired destination can however, this can be achieved if the substance concerned is SF-1293 in an amount of 25 - 600 g

2
per 1000 m for perennial weeds under

10 1 m height (e.g. Artemisia Princeps, Rumex japonicus,

Cyperus rotundus etc.); 75 - 750 g

ρ
per 1000 m in perennial weeds over 1 m in height (e.g. Sasa nipponica, Miscanthus sinensis etc.) and in small bushes (e.g.

Rhododendron haempferi, Rubus crataegifolins etc.)

2 proved to be beneficial; 150 - 1500 g per 1000 m are for large bushes (e.g. Castanea crenata, Quercus serrata, etc.) as well as for controlling fresh sprouts from large stumps.

The preparations containing mixtures of the compounds (A) and (B) can also be used in the usual Forms including aqueous solutions, dusts, wettable powders, emulsions, granules and granules can be produced, in which case also any known solid or liquid Diluents and carriers can be used, as detailed above has been described.

The present invention is illustrated in further detail by means of the following examples. All percentages given relate to percent by weight, unless not something else is expressly stated. So far in

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the examples monosubstituted salts of
Substance SF-1293 are mentioned, it is
around the corresponding phosphate (only M in the formula (I) given above is a cation and M
is a hydrogen atom).

Examples 1-3 explain the preparation of the mixtures or preparations according to the present invention.

Example 1 10 Aqueous solution

1a) Substance SF-1293 (free acid). 30.00 %

Octylphenylpolyoxyethanol 15.00 %

Methyl para-hydroxybenzoate 0.15 %

Water 54.85 %

1b) monosodium salt of SF-1293 10.00 %

CMH 20.00 %

Octylphenylpolyoxyethanol 15.00 %

Methyl para-hydroxybenzoate 0.15 %

Water 54.85 %

The ingredients listed above under 1a) and 1b) are mixed together so that
results in an aqueous solution which can be further diluted prior to use, ie prior to application to the foliage of the plants.

25 Example 2

Wettable powders

2a) Substance SF-1293 (free acid) 50.0% Kieseiguhr 45.0 %

Monoorbitan alkyl esters
(as surfactant) 5.0 %

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11/1/1978 % 2b) mono- (diethanolamine) salt % the substance SF-1293 15.0 % 2,4-D (Na salt) 30.0 % Kieseiguhr 50.0 Monosorbitan alkyl esters 5.0

The ingredients listed above under 2a) and 2b) are evenly divided into those specified Amounts mixed together and finely ground so that a wettable powder is obtained which is easily in Water dispersible and suitable for spraying on foliage.

Example 3 Dustable powder

3a) Substance SF-1293 (free acid) 5 % talc 95 %

3b) monoisopropylamine salt of

Substance SF-1293 5.0%

Dowco-233 (Na-SaIz) 5.0 %

Talc 90.0%

The ingredients mentioned above under 3a) and 3b) are used in the specified proportions mixed and ground evenly. The powder created in this way can be used directly on the foliage of the plants are dusted on

preferably in an amount of 0.4 - 6 kg per 1000 m

In the following Examples 4-8, the herbicidal properties of the substances SF-1293 explained.

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Example 4

Try to apply before rising

Highland soil was placed in a pot with a diameter of 10 cm, in which then in a depth of 1 cm seeds of Digitaria adscendens (fingergrass) were sown .. After light pressing the soil surface became the soil evenly with solutions of the sodium salt of the substance SF-1293, which had been dissolved in 5 ml of water in different concentrations, sprayed. 10 Days after spraying, the number of fingergrass seedlings and the percentage prevention were determined of rising found in comparison with untreated pots. For comparison were also experiments using glyphosate instead of the sodium salt of the substance SF-1293 carried out. The results are compiled in Table 2 below.

Table 2

Percentage prevention of opening

Trial connections

applied amount g / 1000 m '0 100 250 500

SF-1293 (Na-SaIz)

lyphosate (isopropylamine salt) (control)

95

100

100

909819/0308

- 9Q-

11/1/1978

Example 5

Try post- rise treatment

Highland soil was placed in a pot with a diameter of 10 cm. In the earth were in sown fingergrass seeds at a depth of 1 cm from the surface of the soil. Once the seedlings have a Had reached a height of about 10 cm, 1.2 ml -

(corresponding to an amount of 100 1 per 1000 m) 10 of an aqueous solution of the test compounds in different Concentrations on the foliage according to the information in Table 3 below sprayed on. 10 days after the treatment, the damage to the plants was revealed by inspection determined using a scale of 0-10; according to the scale, 0 means no effect and 10 means complete Mortification.

The details of this scale rating were as follows:

Percentage leaf damage scale

0 0 %

1 10%

2 20%

3 30 %

4 40%

5 50%

6 60%

7 70%

8 80 %

9 90 % 100 %

809819/0908

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The test results are compiled in Table 3 below.

Table 3

Extent c 8th 0.1 Trial connections ler damage 10 10 SF-1293 (Na-SaIz) Concentration (ppm)
0 0.01 0.03 VJl 10 SF-1293
(Dimethylamine salt) 0 1 10
I. Glyphosate (isopropyl
amine salt) (control) 0 3 0 0

The above table shows that the organic amine salt of Substance SF-1293 has an increased herbicidal effect Has an effect.

Example 6

Aqueous solutions containing the sodium salt of the substance SF-1293 in various concentrations, as shown in the following Table 4, and to which 0.1 % octylphenyl polyoxyethanol was further added as a surfactant, were used in an amount

from 150 1 per 1000 m directly to naturally occurring perennial weeds applied in the growth stages indicated in Table 4. 7 days or Fourteen days after the foliage treatment, the extent of the damage to the plants was visualized on a scale from 0-5, in

9098 19/0908

Percentage leaf damage % 0 % 20th % 40 % 60 % 80 100

11/1/1978

which O means no effect and 5 means complete kill. In detail, the evaluation was made as follows done like this:

Scale 0 1 2 3 4 5

One month after the treatment, the suppression of an offspring was determined, the evaluation being carried out as follows: the sign (-) means no offspring, ie complete suppression of the offspring; the sign (-) clearly noticeable suppression of an offspring; dr? 10 signs (+) significant suppression of a child; the sign (++) mean suppression of the offspring; the sign. (+++) no suppression of offspring.

The results of the tests are compiled in Table 4 below. In all of the following tables SF-1293 means the monosodium salt of the substance SF-1293.

9 09819/0908

Tabel

O CO O>

Wax-
tumultuous
stage
(cm) Extent of damage 5 glyphosate
(Isopropyl
amine salt) ■ 0 ^ 2 after 14 days 0.2 glyphosate
(I.sopropyl-
amine salt ") 0.2 ■ Suppression of the
Offspring - glyphosate
(Isopropyl
amine salt) 0.2 Ver
SjJ ch s-
P'flan-
z en 100 after 7 days 5 0.1 2 SF-1293
(Na-SaIz) 5 0.1 3.5 after a month - OA + Pc 70 SF-1293
(Na-SaIz) 5 1 4th 0A \ 5 2 5 SF-1293
(Na-SaIz) - + - Ht 50 0A% 0.2 5 3 4.5 4th 5 4th 4.5 OjI j 0.2 - - - Ap 30th 4th 5 3 2 5 5 3 2 - - - + Cy 30th 4.5 5 1 2 5 5 1 3 - - + + Ro 80 5 5 1 1.5 5 5 2 3 - - + - Ic 5 m 4th 5 1 3 5 5 1; 5 4th - - + - Pr 120 4th 2 1 5 5 3 3/5 - - - .Ms 4th 0.5 5 2 - + 4th 4th - 4th -

2S48224

11/1/1978

The individual test plants were designated with the following abbreviations:

Pc: pleioblastus chino

Ht: Helianthus tuberosus

Ap: Artemisia princeps

Cy: Cayratia japonica

Ro: Rumex obtusifolius

Ic: Imperata cyrindrica

Pr: Pueraria lobata

Ms: Miscanthus sinensis

It can be clearly seen from Table 4 that when 150 1/1000 m of a solution containing the substance SF-1293 in a concentration of 0.1-0.2 % is applied to wild perennial weeds in the growth stage, complete destruction is achieved , no matter what kind of weed it is. Regrowth of the plant is also completely suppressed.

Example 7

Aqueous solutions which contained the sodium salt of SF-1293 in different concentrations according to the information in Table 5 below and 0.1 % octylphenyl polyoxyethanol as a surface-active agent were used in an amount of 150 l /

ρ
1000 m applied to an area in which various bushes grew wild. One month after the treatment of the foliage, the damage to the plants was assessed visually on a scale of 0-5, where 0 means no effect and 5 means complete destruction, in the same way as is also described in Example 6. The results of the experiment are summarized in Table 5 below.

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posed.

Table 5

Conc
tration Extent of damage Sc Ct Rb Zp . ^Pa Vb Experimental
connect
gene 0.190 Total-
evaluator
tion 4th 4th 5 4th 4th 4th SF-1293
(Na-SaIz) . 0.2 4th 5 5 5 5 5 5 I! 0.3 5 5 5 5 5 5 5 Il 0.1 5 1.5 0.5 1 0 3 2 glyphosate
(isopropyl
amine salt) 0.2 2 4th 0.5 1.5 1 4th 3 Il 0.3 3 4.5 1.5 2 2 4.5 3.5 It 4th 0 0 0 0 0 0 untreated 0

The abbreviations of the test plants have the following meanings:

Sc: Smilax china

Ct: Castanea crenata

Rb: Rubus palmatus

Zp: Zanthoxylum piperitum

Pa: Pteridium aquilinum

Vb: viburnum dilatatum

From Table 5 it can be seen that SF-1293 also has a strong herbicidal action against wood plants, irrespective of the species.

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Example 8

Aqueous solutions which contained the sodium salt of SF-1293 in different concentrations according to the information in Table 6 below and 0.1 % octylphenyl polyoxyethanol as a surface-active agent were used in an amount of 150 1/1000 m on wood plants with a height of about 60 - 70 cm applied. Seven days or 14 days after the treatment, the extent of the damage to the test plants was determined visually, using the same scale (0-5) that was used in the example? is called. The results are shown in Table 6 below.

Table 6

Conc Extent of damage La Ch 1 Cp Ct re ± H4 Ta gene Ct Experimental tration after 7 days 0 0 5 Pd La Ch Cp
j 5 connect
gene 0.12596 Pd 4 _f 5 0 0.5 5 5 5 0 0 5 SF-1293
(Na-Salst) 0.25 " 3.5 4.5 0 0.5 5 5 5 0 1 5 Il 0.5 " 4th 1 0 0 2 5 5 0 2 3 Il 0.125% 4th 1 0 1 2 2 2 1 1 4th glyphosate
(isopropyl
amine salt) 0.25 " 0 2 1 2 3 3 3 3 3 5 Il 0.5 " 1 0 0 0 0 4th 4th 4th 5 0 Il 2 0 0 0 0 untreated 0

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The abbreviations for the test plants have the following meanings:

■ Pd: Picea densiflora

La: Larix leptolepis

Ch: Chamaecyparis obtusa

Cp: Cryptomeria japonica

CT: Castanea crenata

It can be seen from Table 6 that SF-1293 is not phytotoxic against Chamaecyparis obtusa even in an amount of 150 1/1000 m if it is applied in a solution which contains the substance SF-1293 in a concentration of 0.5 % contains; as a result, the substance can be used for the selective control of weeds and bushes in forest areas of this crop.

The following examples 9-15 illustrate the synergistic effects that can be achieved if you use the substances SF-1293 (A) in combination with other herbicidal compounds (B) 15 used.

Example 9

Preparations were made in the form of aqueous solutions containing as active ingredients different salts of SF-1293 (0.05 % or 0.1 %) or

20 CMH (0.3 %) or mixtures thereof and 0.1% Octylpheny lpo lyoxyäth.ano 1 contained as a surfactant. The aqueous solutions were applied in an amount of 100 1/1000 m to Rumex obtusifolius in various stages of growth;

the plants were in the treatment

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Pots with a diameter of 20 cm. 21 days after the foliage treatment, this became The extent of damage to the test plants was determined visually, on a scale of 5 0-5, according to which O means no effect and 5 means complete kill in the manner as this has already been described in Example 6. Another assessment was made four months after treatment made, both in terms of

10 the damage to the plant as well as the suppression of the offspring from the subterranean parts of the plant. The symbols used for the assessment from (-) to (+++) were the same as already explained in Example 6. The experimental

The results are compiled in Table 7 below.

It can be seen from Table 7 that the substances SF-1293 alone when used in a concentration of 0.05-0.1 % are unable to bring about a satisfactory suppression of the offspring and that CMH when used alone neither has a herbicidal effect nor a prevention of the offspring. With the combined use of SF-1293 and CMH, on the other hand, there is a pronounced synergistic effect, so that all parts of the plant above and below ground are killed and offspring from the subterranean root parts of the plant is prevented.

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Table 7

; Extent of damage

ί nacn “after 121 days; 4 months

Test compounds Concentration of SF-1293 salt

0.05% 0.1%; 0.05% j 0.1%

SF-1293 mono Na salt di Na salt "mono-K salt" di-K salt

"Mono (isopropyl ~ amine) salt

"Mono (n-butylamine) salt

ICMH (O ₇ 3%)

2.5
2.5

J2.5

0 'I +++ j Zj 5 : ++ 0 +++ j 2,5! ++ 0

| 3 _; 5

! 4

3 1 + 0 I.

SF-1293

mono-Na salt + CMH (0.396)

di-Na salt + CMH (0.3%)

mono-K salt + CMH (0.3%)

di-K salt + CMH (0

4.5

4.5

■; ■

4.5

| 4 j 4.5 14.5

i I ^r

mono (isopropylamine salt + CMH (0.3%)

mono (n-butylamine) salt + CMH (0.3%)

4 _A 5

! 4.5

untreated

5 0

5 I 5

I j

5 I-

I!

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Example 10

Aqueous solutions containing the substances SF-1293 (A) and one of the compounds (B) separately or contained in a mixture in different concentrations given in Table 8 below,

are in an amount of 100 1/1000 m on Rumex obtusifolius (abbreviated as Ro) and on a grassy one perennial weed, Zoysia japonica (abbreviated as Zy), which grows in a certain

10 stage had been planted in pots and were well rooted in them. 21 days After the treatment of the leaf parts of the plants, the extent of the damage that had occurred was determined visually judged on a scale from 0 to 5, whereby - like this

15 has already been explained in example 6 - 0 means no effect and 5 means complete destruction. 3 months later another offspring suppression assessment was made to a measure for the destruction of the subterranean plant

to have shares; the same symbols as those explained in Example 9 were used for the evaluation have been.

The results of the tests are summarized in Table 8 below, with the Mono-25 sodium salt of SF-1293 the abbreviation "SF" has been used.

909819/0908

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Table 8

j extent of damage,

i after: after

Test compounds (concentration! Days ^: months

in %) I: 1 — Ί——

! IRo: Zy; Ro j Zy

SF (0.05%)
SF (0.1%)
CMH (0.596)
"(0.6%)

"(O., 3%) + SF (0.0596)" (Oj. 596) + SF (0.196) "(0.6%) + SF (0.05%) ¹¹ (0.6%) + SF (0.1%) 2,4-D (Na-Salz) (0.196)

(0.296)

(0.1%) + SF (0.05%) (0.196) + SF (0.1%) (0 _; 2%) + SF (0.05%) (O ₇ 2%) + SF (0, 1%) MCP (Na-Sa] Z-) (O ₇ 1%)
(0.2%)

(0.196) + SF _(0; 05%) (1% O ₇₎ + "(0.1%) (0.2%) +» (O ₇ 05%) (0.2%) + · '. (O ₇ 1%) 3,4-DP (Na-Salz) (0.1%)

(O ₇ 2%)

(0.1%) + SF (0.05%) (O ₇ 1%) + "(0.1%)

909819/0908 3.5; 2.5

4.5-

4.5

4.5

0 • 0 3.5

3.5

4.5 5 0 0

Table 8 (continued)

j 3,4-DP (Na-Salz) (0.2%) + SF (0.0596) = 5 5

j is

i "(Oj2%) +" (0.1%) j 5 i 5

j MCPP (Na salt) (0.1%) ίΐ | θ

I "(0.2%) 2 | θ

ι ^; j

j "(0.196) + SF (0j05%) 4.5 3

j "(0.1%) +» (0.1%) 4.5

¹¹ (O ₇ 2%) + "(Öj 0596) 5 5

¹¹ (O ₇ 2%) + "(0.1%) 5 5

MCPB (Na-Salz) (θ _; 1%) 1 0

¹¹ (0.2%) 2 0

"(0.1%) + SF _(0; 05%) 4.5 3

"(0.1%) +" (0.1%) 4 _; 5 4

"(0.296) +"_(0; 05%) 5 5

, "(0.296) +" (Oj 1%) 5 5

2,4,5-T (Na salt) (0.1%) 10

¹¹ (0.2%) 2 0

(O ₇ 1%) + SF (0.05%) 4.5

(0.2%) + "(0.05%) 5

(0.2%) + »(0.1%) j 5

SL-5O1 (Na salt) (0.1%)

(0.296)

0.5

11/1/1978

(0.1%) + SF (0.05%) U, 5J4 (0.1%) + "(0.1%)

(0.2%) + »(0.05%)

»(0.296) +" (0.1%)

ί 2,3,6-TBA (Na-Salz) (0.1%)

"(0.296)

3.5 3.5

^! 4 _; 5 1
2

Il

(0 ^ 196) + SF (0.05%)
909819/0908

-i-

| 0

I I

Table 8 (continued)

2,3,6-TBA (Na salt) (0.1%) + SF (O _y 1%): 4

(Oj2%) + »(O _r O5% i5

Banvel-D (Na salt) (0 _f l%) il

(0.296) | 2

IAmiben (Na-Salt) (0.1%) I "(0.2%)

+ SF (0.05%) J4 (0.196) + ^{! I} (0.1%) | 4 (0.2%) η- "(0.05%) J5

0 3 4 5 5 0

| 4

(O ₇ 1%) + "(0.196) I4

(0.2%)

_; 05%)

j 2%) + "(0.196) 5

TPA (Na-Salt) (0.196) (0.296)

"(0.1%) + SF _(0; 05%)

"(0.196) +" (0.1%)

+ "(0 _; 05%)

!1

| Dowco-233 (sodium salt) (0 ₇ 05%)! 3

j

"(Oj1%) 'j 4

(OjO5%) + SF (O, O5%) .'5

^{; I} (0.05%) + ^{; I} (O ₇ 1%) | 5

3 3 5 5 0 0

3 5 5 0 0

11/1/1978

5 5 0 I +++

j2 | O I +++

3.5

(0.1%) + »(0.05%)! 5

ί ι

(0 _; 196) + "(0 _; l%) j 5 \ 5

90981 9 / 090Ö

Table 8 (continued)

11/1/1978

Glyphosate _{[Q O59} , -v η 5 ι

(Isopropylamine salt) ^v 'ί ϊ ■

2.5 2 -

(0.05%) + SF L (0j05%) ^A.

(0.05%) + SF (0 _; l%) 5 (0.1%) + SF (0 _; 05%) 5

DPX-1108 (Na salt) (0.2%)

(0.4%) "(0.2%) + SF (0.05%)

¹¹ (0.4%) + SF (0.05%)

¹¹ (0.4%) + SF (C.

NP-48 (0.1596)

"(0.1596) + SF (0.05%)

¹¹ (0.3%) + "(0.1%)

Linuron (0.1%)

¹¹ (0.3%)

»(0.1%) + SF (0j05%)

¹¹ (0.396) + "(0.156)

.5:

S5I -

3 _r 5 .5

2; 3 3/5 4

2 _r 5

3.5

4 _; 5

4.5

3.5

4 5 5 5

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11/1/1978

Table 8 (continued)

iATA (0.05%)

\ »(0.05%) + SF (0.05%)

i "(0.05%) +" (0.1%)

j ^{; I} (0.1%) + "(0.05%)

»(O ₇ 1%) + ^fI (0 _; l%)! Choline hydrochloride (0.1%) ^i! (0.2ft)

(O _f lft) + SF (O ₇ 05%)

IV) +++ - 4th +++ j +++ - 4th 5 5 -

(0.1%) + 3Ρ (0µ%) 4 _; 5ί 4 K ^ St ^SP J ₅ 5

%} δ

ethylamine hydrochloride (0.1%) 0

(O ₇ 2ft) jo

(O _f l%) + SF L (0; 05%) ³

(O _? 1%) + SF

(0 _f 2%) + SF (0.05ft)

(0 _? 2%) + SF I.

5

0 0

2 _; 5 3 _r 5 4 _V 5

(ojift)

5

untreated

I-

an asterisk (*) means delay in height growth

909819/0908

- ^ r- November 1, 1978

From Table 8 it can be seen that when either SF-1293 (A) or one of the compounds was applied (B) on Rumex obtusifolius and Zoysia japonica alone, considerable damage to the leaf parts of these Weeds is achieved, however, that only a very slight suppression of the offspring from the underground Root parts can be achieved; with the combined use of the two components (A) and (B), however, a complete suppression "of the offspring can also be achieved.

Example 11

Aqueous solutions containing the monosodium salt of SF-1293 and CMH, mixed or alone, as well as 0.1% Octylphenyl polyoxyethanol contained as a surfactant were used in an amount of 1501/1000 m applied to wild perennial weeds at a certain stage of growth. The judgment the damage to the plants (21 days after the treatment) and the suppression of the offspring (after 4 months

20 nates) was carried out in the same way as in the example 10 specified. The results are compiled in Table 9 below.

909819/0908

Tabel Extent of damage

GO O CD

after 21 days

Test compounds (concentration in %) (Na salt) (0.05%) 5%) untreated l · CMH (0.3%) Pc 5 Ap Ro Cy ic; Pr 5 At Sc Cp Ch SF-1293 (0.1%) 5%) f " (0.6%) 2 5 4th 2.5 3 4th 3 1 3 1 5 i! (0.2%) (Na salt) (0.05%) - f " (0.3%) 4th Ul Δ 4th 4, 2 4th 2 5 il (0.4%) (0.05%) ■ f " (0.6%) 5 5 5 5 5 5 3 5 3 5 ; ϊ (0.1%) - + · ^I! (0.3%) 5 5 5 5 5 5 ^> 5 5 4.5 5 CMH (0 ,; (0.1%) ■ + · " (0.6%) 0 1 0 0 0 0 5 0 0 0 1 "(Ο, ί (0.2%) 2 2 0 1 1 1 0 1 0 3 SF-1293 (O ₇ 296) 3, 5 4.5 4th 4.5 4, 3 4th 2 5 « 4 _; 5 4.5 4th 5 5 3 4th 2 5 it 5 5 5 4.5 5 5 4th 5 4th 5 Ii 5 5 5 5 5 .5 4th 5 4th 5 .1 5 5 5 5 5 5 5 5 5 5 ϊ! 5 5 5 5 5 C, 5 5 5 5 0 O 0 0 0 0 0 0 0 0

CD CD O OO

Table 9 (continued)

Test compounds (concentration in %)

SF-1293 (Na salt) (0.05%)

"(O _T 196)

"(0.496) CMH (O _r 396) ^{! I} (0.696)

SF-1293 (Na-Salt) (0.0596) + CMH (0.396)

»(0.0596) +" (0.696)

(0.196) (0.196) (O _; 296) (0.296)

(0.396) (0.690) (0.396) (0.696)

untreated

Extent d <after 4 Mi

he injury

lönaten

Ap

Ro

Cy

Ic! Pr

To j

Sc ι Cp I Ch

-ι

00

00 K)

03

- JtT- 11/1/1978

The following abbreviations have been assigned to the test plants:

PC: pleioblastus chino

Ap: Artemisia princeps

Ro: Rumex obtusifolius

Cy: Cayratia japonica

Ic: Imperata cyrindrica

Pr: Pueraria lobata

To: Athyrium nipinicium

Sc: Solanum carolinens

Cp: Cyperus rotundus

Ch: Calystegia hederacea

From Table 9 it is clear that the mixture of the monosodium salt of SF-1293 and CMH to one 5 leads to a considerable improvement in terms of the suppression of the offspring and a broader spectrum of action with regard to the weeds to be controlled Has.

Example 12

10 approaches in the form of aqueous solutions, accordingly those of Example 11, were used in an amount of 150 l /

ρ
m applied to plants that are in one with

Chamaecyparis obtusa planted area ivuchsen. 30 days and 3 months after the treatment of the foliage parts of the plants, the extent of the damage was determined the same determined visually on the scale from 0-5, with 0 again having no effect and 5 complete Killing means, as explained in Example 6. The results are shown in Table 10.

909819/0908

Tabel

co ο co

CD CO O

(0 + CMH (0.25%) nact extent the Taffeta Ms damage after 3 Ct Months Ms Rc (0 + " (0.5%) Ch ι 30 Sat 3 Ch 3 -Sa, 2 3 (0 (1.0%) O Ct 3 4th Rc 0 4th 2 3 4th + " (0.25%) O 5 4th 5 4th 0 5 3 4th 5 Trial connector + I! (O ₅ 5%) O 5 5 0 4.5 0 0 4th 0 0 SF-1293 (Na-SaIz) + " (1.0%) O 5 0 1 5 0 0 0 0 1 η- (0 + " (0.25%) O 0 1 2 0 0 1 1 1 2 η (0 (0.5%) O 1 2 4th 1 0 5 4th 4 _; 5 'CMH (0.25%) (0 (1,056) O 3 4th 4th 2 0 5 4.5 4.5 5 ¹¹ (O ₇ 5%) (0 O 5 4th 4th 4 _; 5 0 5 5 5 5 "(1,096) (0 O 5 4j5 4.5 4.5 0 5 5 4 _j5 5 SF-1293 (Na-SaIz) (0 O 5 5 5 4.5 0 5 5 5 5 ; t (0 O 5 5 5 · 5 0 5 5 5 5 (0 O 5 5 5 5 0 5 5 5 5 (0 O 5 5 5 5 ■ 0 5 5 5 5 O 5 5 5 5 0 5 5 5 5 ii O 5 ■ ρ- 0 5 0 0 5 0 0 H O 5 0 5 0 0 Ii O 0 ίϊ untreated ι (concentration in%) , 125%) , 25%) , 5%) , 125%) , 125%) , 125%) , 25%) _f 25%) , 25%) , 5%) , 5%) , 5%)

SO'

11/1/1978 The names of the test plants were given the following

Abbreviations: Chamaecyparis obtusa Ch: Castamea crenata Ct: Sasa nipponica Sa: Miscanthus sinensis Ms: Rubus crataegifolius Rc:

From Table 10 it can be seen that the mixture of the monosodium salt of SP-1293 and CMH was very significant the anti-offspring effect of the sodium salt increases, but is not phytotoxic against the timber plant Chamaecyparis obtusa.

Example 15

Approaches in the form of aqueous solutions, corresponding to those that had been used in Example 11, were in an amount of 100 1/1000 m on wild weeds, Echinochloa crusgalli (abbreviated Ec) and Digitaria adscendens (abbreviated Dg), applied in a medium growth stage. 14 days as well as one month after the treatment of the foliage parts of the plants, the degree of damage to the plants was determined certainly. One month after the treatment, the size of the offspring in the evaluated in Example 11 explained manner. The results of the investigations are summarized in Table 11.

909819/0908

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Table 11

i Extent of damage ^j

after

Test compounds (concentration in%)

after

Ec ^: Dg; Ec

Dg

SF-1293 (Na salt) (0.05%) j3 i 3

^! 4th

JO

I untreated

; CMH (0.3%)

"(0.696) ■! L

ί jSF-1293 (Na-Salz) (0.0596) + CMH (Oj396) j4

j "(0.05%) + ^i! (0.696) i4

"(0.196) +" (Oj6%) | 5

"(0.296) +" (0.6%) J5 j 5

15th

i i ■

909819/0908

28Λ8224

Example 14

1.11.197a

An area where various wild bushes and weeds were present was in

4 m in size divided into pieces that were evenly sprayed in autumn with aqueous solutions containing the sodium salt of the substance SF-1293 and CMH, alone or in a mixture, as well as 0.1 % octylphenyl polyoxyethanol as a surface-active agent; the solutions were in an amount of 150 1/1000 m

10 used. 7 months after the spraying, i.e. at the end of the next spring, the extent of the Damage to the plants was assessed visually on the scale from 0-5, in which 0 no effect and 5 complete killing as well as complete suppression

15 of the offspring mean. The results are shown in Table 12.

The following names were chosen for the test plants used:

Hd: Hydrangea hirta

Fr: Fraxinus japonica

Rh: Rhododendron kaempferi

Pc: pleioblastus chino

Qu: Quercus grossesenata

Cb: Clethra barbinervis

Hm: Hamamelis japonica

Ct: Castanea crenata

Rt: Rhus trichocarpa

Sy: Styrax japonica

Ln: Lyonia neziki

On: Acer mono

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- 29Γ-

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Tabel 12th Remarks r (Concentration in $) Extent d.
Damaging. Hd 5, Fr 3, Rh 5, Pc 4.5 SF-1293 (Na-SaIz)
(0.125 / 4 Qu 5, Ob 4,5, Fr 4 "(0.25 / °) 4.5 Hd 5, Ob 5, Rh 5 ¹¹ ($ 0.5) 5 Whether 0.5-, Rh 1.5-2, Hm 1.5 CMH ($ 0.5) 0.5-1 Qu 3.5-4, Rh 3.5-4, Cb 0.5
slight damage to
their plants ^{0 ö} "($ 1.0) 1 Ot 3 * 5-4, Ob 1, Rt 1
slight damage to
their plants ¹¹ ($ 2.0) 1-1.5 Pc 4.5-5 not essential
Offspring of Sy and Ha SF-1293 (ITa-SaIz)
($ 0.125) + 0MH {$ 0.5) i 4.5 no significant aftermath
grew from Ln, Rh and Pc ¹¹ (0.125 / 0 +
«($ 1.0) 4.5 severe damage to Pe,
Fr, Hd, Am and others »($ 0.125) + ■
¹¹ (2, OuS) 5 no significant aftermath
grew from Cb, Rh, Pc, Fr »($ 0.25) +
»($ 0.5) 4.5 no offspring from Fr,
Rh and Cb ¹¹ ($ 0.25) +
"($ 1.0) 5 no offspring "($ 0.25) +
¹¹ ($ 2.0) 5 no offspring ¹¹ ($ 0.5) +
¹¹ ($ 0.5) 5 no offspring ¹¹ ($ 0.5) +
»($ 1.0) 5 no offspring »($ 0.5) +
¹¹ ($ 2.0) 5 Hd 30cm, Ln 20cm, Whether 50cm
Pc 75cm, Rh 10-20cm,
For 25 cm Control (untreated.
Height of plants > O

90981 9/0908

284S224

11/1/1978

Example 15

In order to determine the herbicidal effect of SF-1293 against evergreen shrubbery, aqueous
Solutions similar to those of Example 14 in an amount of 100 1/1000 m on ternstroemia
gymnanthera, Ligustrum japonicum and Rhaphiolepis umbellata (abbreviated as Tr, Lg and Ru) applied, 5 months after treatment of the foliage of the plants, the extent of the damage was determined visually , the assessment being made in the same way as given in Example 14. The results are shown in Table 13 below.

909819/0908

11/1/1978

Table 13

Trial connections
(Concentration in 96) Extent of damage Tr Ru SF-1293 Sa Salt (O _T 25 #) I « 5 . 5 (0.5 / 0 4.5 Ul 5 CMH (0.55 *) 5 2 2 "(1 ^ 0/0 2 2> 5 2.5 "($ 2.0) 3 3 3 SF-1293 Ua-S alZ ($ 0.25)
+ CMH ($ 0.5) 3.5 5 5 υ (0.25 / 0 + 5 5 5 ¹¹ (0.25 / 0 +
»(2.0 / 0 5 5 Ul ¹¹ (0> $ 5) +
¹¹ (0.5To) 5 5 5 "(0.5 / 0 +
ti h Qw Ul Ul 5 ¹¹ (0.5 / 0 +
¹¹ ($ 2.0) UI 5 5 untreated 5 0 0 0

909819/0908

11/1/1978

Example 16

Aqueous solutions containing the sodium salt of SF-1293 as the active ingredient and 0.1% octylphenyl polyoxyethanol as a surfactant were applied in an amount of 100 1/1000 m on Cyperus serotinus applied, which was placed in a Wagner porcelain pot with a cross-section of 1/5000 a was pulled. The pot treated in this way lasted 3 months parked outdoors. After this time, the tubers were removed from the bottom of the pot and put in a deep petri dish. The dish was placed in a greenhouse to rise. 21st Days later, an evaluation was made in which the prevention of opening after a A scale of 0-5 was rated, with 0 meaning no effect and 5 complete prevention of the opening. The results are shown in Table 14 .

Table 14

Trial connections
(Concentration in%) Degree of prevention
of rising SF-1293 (Na salt) (0.1%) VJl "(0.3%) 5 Glyphosate (isopropylamine
salt) (0.1%) (control) 5 "(0.3%) VJl untreated 0

909819/090 8

Claims (12)

2848274 1 .11 .1978 claims 1. Weedkiller, consisting of the antibiotic SF-1293 of the general formula Η, ν
^{0 Xd} -CH _o -CH _o -CH-CONH-CH-CONH-CH-C00H NH ₀ CH, CH, 2 3 3 or a salt of this compound as an active ingredient in admixture with a connecting agent or carrier material. 2. weed killer according to claim 1 ,. characterized in that the active ingredient in an amount of 0.01-50 percent by weight is available. 3. weed killer according to claim 1, characterized in that the active ingredient consists of the monosodium salt of the antibiotic SF-1293. 4. Weedkiller, consisting of one Diluent or carrier material and an active ingredient, which in turn consists of a Mixture of (A) the substance SF-1293 according to claim 1 or a salt of this compound and (B) little- at least one of the connections listed below exists: Choline salt of maleic hydrazide, phenoxy herbicide, benzoic acid herbicide, 2,3,6-trichlorophenylacetic acid and their salts, ((3,5,6-trichloro-2-pyridyl) -oxy) -acetic acid and its salts, N-phosphonomethylglycine and its salts, ethyl carbamoyl phosphate and its salts, 2- (i- 909819/0908 11/1/1978 Allyloxyamino) butylidene-5,5-dimethyl-4-methoxycarbonyl-cyclohexane-1,3-dione, 3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea, 3 - Amino-1,2,4-triazole, choline and diethylamines. 5. weed killer according to claim 4, characterized in that the weight ratio of component (A) to component (B) in the mixture is between 1: 0.2 and 1:20. 6. Owl herb killer according to claim 4, 10 characterized in that the active ingredient in the mixture of components (A) and (B) 0.05 80 percent by weight. 7. weed killer according to claim 4, characterized in that component (B) 15 consists of the choline salt of maleic hydrazide. 8. weed killer according to claim 4, characterized in that the salt of the substance SF-1293 of the general formula / P-CH ₀ -CH ₀ -CH-CONH-CH-CONh-CH-COO (MT) (M ¹ ) 0 NH ₂ CH ₃ CH, nA (I) 1 corresponds to 2, in which M and M are equal or different 20 can be separated and each have a hydrogen atom or a cation such as sodium, potassium, lithium. Copper, magnesium, calcium »zinc, nickel or manganese or an ammonium cation which is either is not substituted or by one, two, three or four lower alkyl, hydroxyalkyl, especially hydroxyethyl or lower alkenyl groups 90981 9/0908 ^ "11/1/1978 is substituted, A is an inorganic or organic acid such as hydrochloric acid, Sulfuric acid, hydrobromic acid, phosphoric acid , Perchloric acid, nitric acid, acetic acid, propionic acid, citric acid, 'tartaric acid, Represents monochloroacetic acid, trichloroacetic acid or trifluoroacetic acid, η the numbers 0.1 / 2 or 1 and ρ and q are the inverse numbers 1 2 values of the valences of M and M respectively. 9. A method for destroying unwanted plants, characterized in that one is on the plants or a sufficient amount of the antibiotic SF-1293 according to claim 1 on its growth medium or a salt of this compound applies. 10. The method according to claim 8, characterized in that that the antibiotic SF-1293 was applied in an amount of 25 g - 3000 g / 1000 m (10Ar) 11. The method according to claim 8, characterized in that that the antibiotic SF-1293 is applied in a mixture with at least one of the following compounds becomes: choline salt of maleic acid hydrazide, phenoxy herbicides, benzoic acid herbicides, 2,3,6-trichlorophenylacetic acid and their salts, ((3,5,6-trichloro-2-pyridyl) -oxy) -acetic acid and its salts, N-phosphonomethylglyein and its salts, Ethylcarbamoylphosphoric acid and its salts, 2- (1-allyloxyamino) -butylidene-5, S-dimethyl-A-methoxycarbonyl-cyclohexane-1,3-dione, 3- (3,4-dichlorophenyl) -1-methoxy-1-methy! Urea, 3-amino-1,2,4-tri- 30 azole, choline and diethylamine. 909819/0909 11/1/1978 12. Method for the selective control of
Weeds and bushes in the growing area
of Chamaecyparis obtusa, characterized in that a sufficient amount of the antibiotic SF-1293 or a salt thereof is applied. 909819/0908